5, 5&#39;-dialkylhydantoin-formaldehyde resin aerosol hair spray



,5 -DIALKYLHYDANTOINFORMALDEHYDE RESIN AEROSOL HAIR SPRAY Samuel Grant, Glencoe, Ill., assignor to Helene filurtis Industries, Inc., Chicago, 111., a corporation of Illinois No Drawing. Filed June 1, 1956, Ser. No. 588,622

6 Claims. ((31. 16'787.1)

The present invention relates to a novel hair fixative composition adapted to be applied to the coiifure for holding the hair in place. This application is a continuation in part of my application filed March 25, 1955, Serial No. 496,680, and now abandoned for Hair Fixative Composition, Process and Article of Manufacture.

Hair fixative compositions as heretofore proposed incorporate either shellac or polyvinyl pyrrolidone as the active hair fixative composition. Shellac has desirable properties, but has the disadvantages that it stiffens the hair, and also after it has been applied to the hair, if the hair is combed or brushed, the fixative action is lost. On the other hand, polyvinyl pyrrolidone has the advantage that its fixative action may be restored by passing a moist comb or brush through the hair, because the polyvinyl pyrrolidone is dissolved or softened by the moisture, and its fixative action is restored upon evaporation of the moisture therefrom.

Heretofore, the only commercially feasible resin which has been employed in hair fixative compositions having the characteristic of rejuvenation by moisture has been polyvinyl pyrrolidone. However, such compositions present several distinct disadvantages. Because of the hygroscopicity of the polyvinyl pyrrolidone it loses its fixative qualities on the hair in humid atmospheres, such as occur in many parts of the country, so that the duration of its fixative qualities are relatively limited. Furthermore, when incorporated in aerosol compositions together with a propellant as for example one or more of the Freons in a pressure tight container, deterioration of the composition occurs in the container and corrosion of the container occurs. Whether corrosion of the container is the result of deterioration of the composition, or deterioration of the composition is brought about by the chemical action involved in the corrosion is not known. The reaction which occurs in the container frequently results in destruction of the perfume and the development of malodor, and the weakening of the container by the corrosive attack renders the container unsafe for use after a relatively short period of storage. The corrosion and deterioration appeared to be accelerated by the relatively high temperatures which are often encountered in storage of such containers during the summer season. In addition, the polyvinyl pyrrolidone is quite expensive.

It is an object of the present invention to provide a hair fixative composition capable of being applied to the hair as a lotion or fine spray, and which has the characteristics that it holds the hair in place without imparting excessive stiffness to the hair, and is relatively insensitive to high humidity conditions.

A further object is the provision of a hair fixative composition which provides a relatively hard coating resistant to scraping or rubbing, is relatively non-hygroscopic, and which has sufficient water solubility so that its action on the hair may be rejuvenated by brushing with a moist comb or brush.

A further object is the provision of a hair fixative com- 2,956,927 Patented Oct. 18, 1960 position which is compatible in a mixture of a lower aliphatic volatile alcohol, and a Freon, and which is stable in storage in contact with a tin or steel surface container.

A further object is the provision of a hair fixative composition which is compatible in a mixture of Freon and alcohol, is relatively non-hygroscopic, is relatively inexpensive, and which can be washed from the hair with water.

According to the present invention, I prepare a hair fixative composition incorporating a 5-position substituted hydantoin-formaldehyde resinous condensation product in a vehicle comprising a lower volatile aliphatic alcohol and liquefied Freon.

The compositions of this invention are preferably packaged under autogenous pressure in pressure tight spray valved containers, from which the compositions are applied to the hair as a spray issued through a valve. The valve has a fine orifice and is manually controlled. Such containers are commercially known and need not be described herein. However, aqueous alcoholic solutions of the resin may be employed as a wave setting composition, for holding finger waves or pin curls in place. The compositions of the present invention, when employed in aerosol form, have the advantages that they have low viscosity, are easily applied to the hair, quickly set on the hair so as to hold the hair in place, form coatings which are resistant to abrasion or scraping, and are relatively insensitive to high humidity atmospheres, so that the fixative action is not lost on hot, humid days. The compositions have the further advantages that they may be stored safely over long periods of time in a tinned steel container without danger of decomposition or deterioration and without destructive corrosion to the container. The 5-position substituted hydantoin-formaldehyde resinous compositions furthermore are less expensive than polyvinyl pyrrolidone, heretofore employed in hair fixative compositions of this type.

The 5-position substituted hydantoin-formaldehyde resinous compositions may be prepared in known manner, as for example by reacting substantially one mole of a 5-substitued hydantoin with two moles of formaldehyde, or a formaldehyde yielding substance, under suitable temperature conditions in the presence of a catalyst as disclosed, for example, in Patents 2,155,863 or 2,532,278. The solid resins formed by reaction of formaldehyde with various 5-substituted hydantoins disclosed in said patents may be employed in the compositions of the present invention, the reaction product with the 5,5 dimethyl compound being preferred, because of its low cost, ease of manufacture, and superior properties. Generally, the proportion of such resin is between one and 5 percent of the composition of the present invention, the other ingredients of the composition being a lower volatile aliphatic alcohol as for example, ethyl alcohol, and one or more volatile pressure liquefied fluorochlorohydrocarbons. In addition, the composition may contain a modifying agent, such as for example water solubilized forms or compounds of lanolin, and perfume. The compositions may also contain a plasticizer, if desired.

In preparing the above composition, the resin and perfume are dissolved in the alcohol, the alcohol solution is cooled and is then mixed with the liquefied Freon mixture and other desired ingredients in a suitable insulated tank. The mixture is then transferred into suitable containers equipped with a spray valve for dispensing the composition as a spray.

In the above composition the amount of resin may be varied as desired, and the alcohol may vary between about 1'5 to 50 percent. The selection of the kind :and proportion of Freons employed will depend on the desired pressure characteristics, and the proportion may vary between about 50 to 80 percent by weight. It will be understood that in place of the Freon above specified, other polyhalogenohydrocarbons containing fluorine as one of the halogens may be employed, to produce the desired pressure in the container. Also, other 5- mono or di-substituted hydantoin-formldehyde resins may be employed in place of the 5 .5'-dimethyl derivative. By

the term 5-position substituted hydantoin-formaldehyde resin I include the mono-substituted or di-substituted compounds, and do not exclude such resins modified by an additive or copolymer ingredient.

When the composition is applied to the hair as a spray, the Freon rapidly evaporates, leaving an alcohol solution of the resin on the hair. When the alcohol evaporates the resin becomes set and holds the hair in place.

'As the resin is colorless or light colored, it does not affeet the color of the hair. The lanolin compound present improves the lustre.

Should the hair become disarranged, it can be reset after passing a moist comb or brush through the hair to rejuvenate the resin. The resin becomes reset by evaporation of the moisture therefrom. When the hair is washed, the resin is removed because it is water soluble.

I claim as my invention:

'1. A fixative composition adapted for application to the hair as a spray comprising: a water soluble 5,5'-dialkylhydantoin-formaldehyde resin dispersed in a vehicle, said vehicle comprising a lower volatile aliphatic alcohol and a volatile polyhalogenohydrocarbon of less than three carbon atoms containing fluorine as one of the halogens, the resin being at least about one percent of the composition.

2. A hair fixative composition as specified in claim 1 wherein the 5,5-dialkylhydantoin compound is the 5,5- dimethyl hydantoin.

3. A hair fixative composition as specified in claim 1 wherein said resin is formed by the reaction of approximately one mole of 5,5-dialkyl hyd-antoin with two moles of formaldehyde.

4. A hair fixative composition as specified in claim 1 wherein the proportion of resin is about 1.75 percent by weight of the composition.

5. A composition as specified in claim 1 confined under autogenous pressure in a container equipped with a manually controlled spray valve.

6. A composition as specified in claim 1 wherein the alcohol is ethyl alcohol.

References Cited in the file of this patent UNITED STATES PATENTS 2,155,863 Jacobson Apr. 25, 1939 2,532,278 Chadwick Dec. 5, 1950 2,633,423 Bower et al Mar. 31, 1953 OTHER REFERENCES Downing et al.: Soap and Sanitary Chem, vol. 29, No. 9, pp. 142, 143, 147, 149 and 153 pert.

Hackhs Chem. Dictionary, 3rd ed., McGraw-Hill Book Co., Inc., NC, 1944, 'pp. 416 and 882.

Schimmel Briefs, No. 233, August, 1954 (l p.)

Janistyn: Reichstoife, Seifen, Kosmetika, vol. 2, 1950, pp. 159-64, esp. p. 163, Huthig Verlag, Heidelberg.

Elchem-1124, Dimethyl Hydantoin-Forrnaldehyde Resin (DMHIF), Du Pont New Products BulL, No. 26, July 29, 1948, 3 pp.

Chem. and Eng. News, Nov. 3, 1947, p. 3243.

Mfg. Chemist, January, 1954, pp. 23-25. 

1. A FIXATIVE COMPOSITION ADAPTED FOR APPLICATION TO THE HAIR AS A SPRAY COMPRISING: A WATER SOLUBLE 5,5''-DIALKYLHYDANTOIN-FORMALDEHYDE RESIN DISPERSED IN A VEHICLE, SAID VEHICLE COMPRISING A LOWER VOLATILE ALIPHATIC ALCOHOL AND A VOLATILE POLYHALOGENOHYDROCARBON OF LESS THAN THREE CARBON ATOMS CONTAINING FLUORINE AS ONE OF THE HALOGENS, THE RESIN BEING AT LEAST ABOUT ONE PERCENT OF THE COMPOSITION. 